Rise of the Brave Tangled Dragons: A D&D Adventure
by Clueless5point0
Summary: Four teenagers find themselves without a home, but maybe they can make a new home together. Merida and Hiccup ran away from situations they felt they couldn't fix, Rapunzel endured a tragedy, and Jack was tasked with bringing joy back into their lives. The four face monsters, their pasts, and an uncertain future. Based loosely off of D&D monsters and abilities.
1. New Beginnings

**Authors Note: Hey guys! This is my first story on fanfiction, but I've been wanting to write it for a long time. The pasts of Merida, Jack, Hiccup, and Rapunzel will be revealed throughout the story, as what happens to them isn't identical to the movies. Thanks for reading, and I hope you enjoy! Please review, and feel free to suggest plot threads that you may want to be explored.**

 _************************************************************ Jack **************************************************************_

 _Darkness. That's the first thing I remember. It was dark, and it was cold, and I was scared._

He was underwater, rising up toward the surface, and yet even though he was immersed in liquid he could feel what he thought was a tear make its way from the corner of his eye. And then he saw the Moon. It was so big, and so bright, it seemed to chase the darkness away. As he broke through the surface of the ice, he continued to look up at the Moon, wondering if it was going to explain anything or just leave him there, wondering why.

 _Your name is Jack Frost. You need to bring joy back into the lives of three very special people, and in doing so, you may just find out something about yourself._

The cryptic message didn't explain anything, of course, and as Jack felt himself being lowered back onto the surface of the ice, he was surprised to find it reforming beneath his feet. Chuckling, he went to take a step on the slippery ice, but his foot hit something. Looking down, he saw that it was a staff, straight most of its length until the end where it curved into a hook. Curious, he poked it with one foot, and a burst of frost originating from where he'd touched it appeared on the staff. As he picked it up to examine it, the staff vibrated and he could see patterns of frost appearing where the end had touched the ice behind him.

Amazed, the white-haired teen tapped a tree with it, and was ecstatic to find the same frosty patterns appear on the bark. Laughing, he began to run in circles around the pond, spreading the beautiful creations across its surface. All of a sudden, he felt himself lifted into the air by a cold wind. Crying out in surprise, he struggled to position himself upright and saw the pond from above, the frost spread out across the ice. The moment didn't last long, however, because the wind suddenly stopped, and he fell quickly and landed on a tree branch not too far off the ground. Sitting back up, he grinned. He didn't know much, but he knew his name was Jack Frost and that he had ice powers.

He jumped down, noticing that the wind slowed his fall, and spent a while practicing with the staff. He could do all sorts of things, from creating frost to shooting blasts of ice to flying. The bigger stuff, he noticed, could only be done a few times before he was too tired to do them anymore. He steadily progressed in his attempts to use the wind to fly, because for some reason it seemed to him like he already knew how, almost like muscle memory. Or maybe, it just meant he was made to do this. At this point he'd effectively tired himself out, and he knew that if he wasn't focusing on something else that he would just wonder about the strange situation he'd found himself in. He had just found himself rising up from under a frozen pond; he had ice powers. His name was Jack Frost, and he was supposed to make three people happy again to learn about himself. The list of things he knew was certainly short. He couldn't remember anything from before that moment in the pond, so maybe he had been created to help these people. Tomorrow he'd start looking for them, but for now, he was tired. He flew up to a large, sturdy looking branch on a nearby tree and put his back to the trunk. There was no snow around like he expected, but nonetheless, he fell asleep, frost spreading out from where he sat to cover the entire tree.

 _~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Rapunzel ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~_

Rapunzel stooped down to pick up the trailing end of her massive head of hair. The golden locks were far from what she'd call manageable, but she knew that her struggles would be worth it when she finally got to see Eugene again. Her eyes moistened as she thought about what had happened to him, but she swiped her hand across her face and continued. She could grieve more later, but for now she had to get out of here before Gothel woke up. Ideally, she would never have to see Gothel again.

"I can do this, I just need to find an adventuring party and then then I'll be able to figure out what is going on," she said, trying to motivate herself. Pascal, a small chameleon she'd befriended during the 18 years of her imprisonment, squeaked in encouragement from his perch on her shoulder. She secured her awkward handhold on her hair and continued to walk through the forest, trying to remember the way for future reference. She sniffled as she thought about how she'd never had to worry about navigating when Eugene was around, but she shoved aside thoughts of him and tried to focus on the task at hand.

She'd only recently gotten out of the tower where she'd spent most of her life, and so she really had no idea where she was going. She just knew that she was looking for an adventuring party, and that the party needed to move out fast, before Gothel could show up. At the thought of meeting new people and getting to see a new place, Rapunzel's optimistic attitude was surfacing even as she grieved, and she hummed to herself as she walked, hoping to run into who she needed to find. She had a feeling that it'd happen pretty soon. Who or whatever had given her these powers had likely done it for a reason, and what better reason was there than being an adventurer and helping people?

First things first, she needed some new clothes, as her lilac gown was getting dirty from travel, and it wasn't exactly the most practical outfit for adventuring. Glad to have some sort of easily attainable goal for the moment, Rapunzel set her sights on finding a village nearby where she could obtain some gear and food.

 _xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx Merida xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx_

Merida walked into the small village leading Angus, her horse, along behind her. She wore her longbow across her shoulders and had a quiver of arrows at her back, along with a sword sheathed at her side. Her gowns long exchanged for practical cotton breeches and shifts dyed dark greens and browns, she was the perfect picture of a woods dweller. However, no matter what she did, she could never completely leave her heritage behind. Her unruly red hair tumbled down past her shoulders, earning her plenty of glances from the townsfolk, most of whom had dark hair and eyes.

Merida greeted the few people she knew as she passed, but none of them stopped to talk, and she didn't expect them to. She was the foreigner who came here sometimes to trade, not a good friend.

She made her way to the marketplace and got what she needed, trading some rare herbs she'd collected in her travels for some oats for Angus, rope, and a new water skin. She was about to leave when a thought occurred to her. She'd been wanting some company, and she was never going to find any unless she did something to meet people. She looked around, searching for someone she knew at least somewhat.

"I was just wondering," she started, directing her words to the man she'd just gotten the new rope from, "If you'd seen any other… folks like me around here? Like me as in loners who are comfortable in the woods?" She quickly stopped as she realized she didn't exactly know who she was looking for. Just some people who'd accept her and be all right with traveling and fighting monsters… A realization hit her as her thoughts sank in. "Any adventuring types?" she added.

The man chuckled. "Well, there aren't too many around these parts, but you might look out for Hiccup, he just came through a day or two ago."

"Excuse me?" she asked, confused.

"His name is Hiccup." Merida let out a very unladylike snort but motioned for the man to continue as she struggled to regain her composure.

"He's a real outdoorsy type like you, always wandering around, not too bad with weapons. He's got a real bond with nature, I hear. A good lad too, he helped out our blacksmith when the poor guy was swamped with orders for new weapons for the royal guards."

She raised an eyebrow. This Hiccup didn't seem too bad, even if his name was hilarious.

"Do you know where he might be? If he's anything like me it'll probably be hard to find him once he's back in the woods, so I'd like to at least have a place to start."

The man thought for a moment before answering. "He said something about heading to Burgess after he was done here, you might check there."

Merida nodded. That'd make sense, to go to the bigger town before heading back into the wilderness for a while, she'd done it before. "Thank you, I'll keep an eye out for him. What did you say your name was?"

The helpful vendor laughed. "Getting all sociable now are you, Miss Merida?"

Merida grinned and responded, "No, but everyone's got to have friends somewhere, right?"

"I suppose so. And the name's Flint."

As she walked away, Merida was really excited for the first time in a while. For the first time since she'd left, she'd have friends, people to talk to. She may not find Hiccup this time, but if she kept asking around, she'd be sure to find him eventually. And in the meantime, she could keep looking for other adventurers in need of company. She mounted Angus, and urging him into a fast trot, set off for Burgess.


	2. Accidental Mischief

**Author's Note: Hey again guys! It's been a week, so here's chapter 2 for your reading pleasure.** **Thanks so much to all of you who reviewed, favorited, and followed, I really appreciate it! Reviews are especially awesome, since I can see what you guys think of the story and my writing. Don't be afraid to just comment your thoughts or say hi!**

 **Anyways, here's the first bit of the story with Hiccup- I hope that I did him justice, enjoy!**

Hiccup finished packing up his campsite, and after a moment of hesitation, he donned a simple brown cloak instead of his normal brown vest. It was warmer than usual for this time of year, and yet sometimes he still habitually put on his warmer clothes in preparation for going outside into the harsh cold of Berk. Looking over his shoulder at Toothless, he knew it had been worth it, but it was still hard sometimes. He missed his family, and his friends. He'd left his whole life behind to save his best friend, and he still wished he'd never had to choose.

"We're gonna have to walk today buddy," he told Toothless. "We're too close to Burgess and whatever little towns are around here to risk someone seeing us." Toothless looked disappointed, but Hiccup knew he understood. Seeing a dragon would cause most reasonable town watchmen to sound an alarm, and he certainly didn't need the town up in arms when he got there to buy supplies. He hadn't been able to explain to his father, so he somehow doubted his ability to explain the situation to armed strangers.

As Hiccup hiked, Toothless walked along beside him, scaring away most of the wildlife. That was a good thing in some cases, as some of the local wildlife was less than friendly, but it was also scaring off any prey that may have been around. Not that he was any good at catching food anyway, he'd found out very early on that he was a horrible archer.

"Toothless, could you go get some food? I'll pick up some stuff in Burgess when I get there, but right now I'm starving," Hiccup said.

Toothless was more than willing to do what he'd done for Hiccup for a while now, and he bounded away through the trees once Hiccup reassured him he'd be alright on his own for a bit. Hiccup continued towards Burgess, hoping to find something interesting while he had a chance to do so without whatever it was hearing him coming from a mile off.

Sure enough, he hadn't walked far at all before he started hearing something. Listening closely, he could hear a series of rapid clicks coming from a nearby marshy area. Curious, he followed the sounds until he pinpointed the exact location, and then he carefully knelt down to look closer. He could feel something tickling his skin and scalp, but he didn't realize what was happening until he caught the full force of an electrical shock.

"Ouch!" he shrieked, jerking his hand back. Unwilling to get shocked and then not find out anything about what had done it, he peered closer at the marshy patch. After a moment of scanning, he saw a small reptilian creature with a pale blue underside and blue-black markings along its back and tail. "Oh man, a shocker lizard," he breathed, in awe of his finding. All too soon, however, he realized that more of the little lizards were congregating, ready to zap him some more. "It's okay, I'm not going to hurt you," he said soothingly, moving back as he did so. The lizards stopped advancing and stared at him, almost as if they understood.

"Thanks for letting me see you guys in action, it was a pleasure," he continued. "That's a pretty good shock you've got there." He looked at the lizards for a few more moments before backing away and saying "I'll leave you alone now." Pulling out his sketchbook, he flipped through numerous pages containing sketches and notes about the various creatures he had encountered in the forest. When he reached a blank page, he made a quick sketch of the lizard and wrote in a brief note about the whole zapping thing before he continued on his way. He had only heard of shocker lizards in books, and the only details he'd gotten were that they lived in marshy areas and used electricity to ward off predators. Happy to have seen another species, he walked on, content to just walk until Toothless got back. Before long, he started hearing crackling again, and was about to start looking for more lizards when he stepped out of the cover of trees and into a clearing occupied by nothing other than a frozen pond.

"What?" Hiccup muttered, more to himself than anything. This was definitely not natural— it wasn't particularly hot outside, but stagnant water should definitely not be freezing. Cautiously advancing further out from the cover of the tree line, Hiccup scanned the surface of the pond. It looked normal, aside from the fact that it was frozen in the middle of summer. And yet, as he stared at it he started to see beautiful patterns of frost making their way across the ice. Hiccup thought for a moment before he decided that he needed to find what was causing this and deal with it before something big happened. That was his job, after all, though self-appointed. He tried to keep nature in balance, which included keeping any powerful forces that might harm it in check, if they couldn't be destroyed outright. A frozen pond in summer was one thing, but the possibility of the unnatural phenomenon spreading was one he couldn't allow.

Deciding against stepping onto the ice for fear of it cracking under him, which honestly was more than probable since the ice shouldn't be there at all, Hiccup made his way around the edge of the pond, looking for any trace of where whatever had caused this had gone. He saw more of the frost on several trees around the pond, and just before he'd gone in a full circle, he found a tree that was entirely encased in frost. He hesitantly touched the tree, just to see what would happen, and it acted just like normal frost, melting a bit under the warmth of his hand. As he pulled his hand back, the frost reformed where he'd melted it, leaving the surface unmarred. Except for the fact that it was there at all, and that it refroze so fast after melting, this appeared to be perfectly normal frost.

 _Is there anything special about this tree in particular?_ Hiccup wondered. Looking back to some of the other trees that had frost on their trunks, he noticed that the frost spread out from a place near his eye level, and didn't reach the tops of the trees. Curious, he looked toward the top of the tree he'd been investigating. Immediately, Hiccup jumped backwards, his hand on the hilt of one of his swords. After a moment, he relaxed his guard a bit, taking a closer look. A young man that looked around his age, maybe 17, sat in the tree, his back to the trunk. He had white hair and pale skin, and he held a crooked staff tightly in one hand. He had on strange brown pants with cords wrapped around his lower legs, and a white shirt covered by a darker brown cloak. Seeming to be unaffected by the cold, the young man was fast asleep.

That… was _really_ not what Hiccup had been expecting. He had been worried that a winter wolf had gotten separated from its pack and made its way down to warmer parts, which would've been bad for everyone involved. Winter wolves were huge, nasty wolves that could freeze you solid with their wintery breath, and if that didn't work they were more than happy to attack you like normal wolves did—with teeth and claws. Hiccup knew he wouldn't have been able to face a winter wolf without Toothless, and even with his dragon around the possibility of him becoming an ice sculpture was on the table.

Hiccup considered his options for a moment. The facts he had currently all pointed to this creature as being the source of the unnatural occurrences in the area. It would be much easier to take care of the threat while it was asleep, whatever it was. Then again, it looked to him like it was just a teenager sleeping in a tree. Hiccup hadn't heard about any creature that could create frost _and_ shapeshift. After some deliberation, he decided to climb a nearby tree to get a closer look at what he was facing before he started swinging any swords around. He edged around the closest tree to the right and was about to start climbing when he heard a familiar sound coming from his left.

"Oh no, not right now," Hiccup whispered anxiously. Trying to get as far away from the strange creature in the tree as quickly as possible, Hiccup backed away towards where he could hear Toothless. On second thought, having his dragon with him when he decided what to do about this whole situation was probably not the worst idea. His dragon burst out into the clearing and right onto the pond. Hiccup waited to hear the loud cracks, but none were forthcoming. Apparently whatever the creature was doing was keeping this place frozen solid. Meanwhile, an oblivious Toothless delivered his catch, a few large fish, and smiled a gummy smile at Hiccup.

"Thanks buddy," Hiccup said quietly, moving to stand beside Toothless on the ice. "But can you try to be quiet, I'm trying not to wake up…" He froze as he saw the teenager, now very awake, sitting in the tree looking from him to Toothless in quiet shock. "…him."

Toothless looked at the pale teenager in the tree, then back to Hiccup in confusion, as if to say _It just looks like another human to me. What's the problem?_ Hiccup, who was now pretty sure that this was an actual teenager rather than some sort of creature, shrugged helplessly. At that moment, the teenager jumped down from the tree, his staff over his shoulder, landing a few paces in front of Hiccup. Hiccup placed his hand on the hilt of his sword again and took a step back, toward Toothless. Noticing Hiccup's motion and the defensive position the dragon had taken up, the teenager quickly put his hands up, his eyes wide.

"Whoa, sorry, I didn't mean to scare you or anything," the teenager said quickly. "It's just that you were standing right there looking at me and I wasn't sure why, so I figured I'd come down and introduce myself." When Hiccup didn't say anything, he continued, his hands still up. "Hi, I'm Jack Frost. Who are you?"


	3. Ice to Meet You

**Author's Note: Hey guys, I can't believe it's been another week already! Thanks so much to everyone who read, reviewed, followed, and favorited this story. I hope you continue to enjoy it, and feel free to review and let me know your thoughts! (By the way, I don't own any of the main characters from the various movies, although I do own various minor characters as well as most of the general plot).**

 **Review Replies:**

 **BrawlerGamer: Your thoughts on the backstories of the main 4 are all really close, but not quite there! I tried to add a twist to each of them so that it was a surprise when their pasts come up in the story. Enjoy some more Hiccup in Chapter 3, and thanks for reviewing!**

 **Guest Reviewer: I did try to make him sarcastic, but it will come up more in other chapters than in this one, I think, because he's worried about Jack being dangerous for now. Next chapter you will definitely get the sarcasm you're hoping for! Thanks for reviewing!**

Hiccup Horrendous Haddock III was still startled, but more by the fact that the teenager standing in front of him looked scared than anything else. He had his hands up in a nonthreatening position, still holding the staff in one hand, and his eyes darted from Hiccup to Toothless, as if he wasn't really sure who to focus on. Hiccup decided to proceed with caution. "My name is Hiccup," he said slowly. "Did you do this?" Hiccup asked, gesturing to the frozen pond and trees.

"Hiccup?" Jack asked, looking like he was going to burst out laughing. When Hiccup narrowed his eyes, hand still on his sword hilt, Jack gulped. "The trees, yes," Jack said. "The pond…" He appeared to think for a moment before continuing. "Maybe indirectly, but no. Except for some frost on the surface I guess," He finally said. Jack turned to look at Toothless, who was growling softly. "Uh… what do you guys want? I wasn't trying to cause any trouble."

Hiccup continued to stare at Jack, still not quite sure how to feel. "So, you froze the trees and maybe the pond? How? Why?"

Now it was Jack's turn to look unsure. "I don't know how exactly, I just used this staff I found." He looked as if he was about to sling the staff over his shoulder again, but he stopped and kept his hands in the air. "For the record, I don't remember freezing this many of the trees. As for why, there wasn't any particular reason. Because it was fun?" Jack looked nervously at Toothless and then back to Hiccup.

Hiccup sighed. "Here's the deal. It's supposed to be summer here right now, there shouldn't be snow or ice or frozen ponds anywhere around here. It's not natural. I can't let you mess around with nature, so can you please just stop with the ice?"

Jack shook his head. "I don't think so," he said quietly. "I'm pretty sure it's part of who I am. Most of who I am, in fact. The frost on these trees will melt, and even if the pond doesn't, it's not causing any harm, is it?"  
Jack had a point, and Hiccup realized he'd been pretty rude so far, not to mention openly hostile. He cleared his throat and took his hand off the hilt of his sword. When he saw Hiccup relax, Toothless stopped growling and sat quietly, content to watch. Hiccup didn't know what was wrong with him, being so rude to this guy he'd just met. Usually those he found messing with nature weren't teenagers. Now that he thought about it, he didn't spend much time with other people anymore.

"I'm sorry, it's just… I try to destroy anything unnatural that is messing with the environment," Hiccup explained. "I overreacted, as long as it doesn't cause any problems we're okay. I was just worried it was going to spread and turn into something bigger. Usually when this kind of stuff happens it's because a dangerous creature is hanging around."

Jack grinned. "You don't think I'm a dangerous creature?" he asked. "For all you know, I'm a creature of mass destruction, who just happens to enjoy naps and surrendering to a guy with a bad hairdo and a dragon." As he spoke, he slowly lowered his hands, looking much more at ease now that Hiccup had relaxed his guard.

Hiccup could tell that Jack was joking, and he had to admit that his concern about Jack being dangerous was all but gone. However, now he was confused about something else. "What's wrong with my hair?" Hiccup asked. He'd always thought it was an unremarkable feature, at best.

"Have you seen yourself?" Jack laughed. "It's sticking out in all directions! I know the humidity around here is pretty bad usually, but still!"

Hiccup tried to catch a glimpse of his reflection in the frozen pond, but the frost covering its surface made it impossible. Eventually he just dragged one of his swortswords out of the sheath at his hip and angled it so he could his hair in the reflection in the blade. Jack was right—it was sticking up at crazy angles. He thought for a second before he remembered the electrical shock so kindly delivered by the shocker lizard he'd encountered a few minutes earlier.

"Yeah, that'd be the work of one of the many actual dangerous creatures around here. You tend to not notice stuff like what your hair looks like when you travel by yourself," Hiccup said. He flattened his hair back down to close to its normal state, and realized with a smile that he'd managed to intimidate Jack while looking like a porcupine. _I wonder what my father would think of me now—I look less like a fishbone every day_ , he thought.

"So you're out here by yourself, guarding against stuff that messes with the environment?" Jack asked. "Sounds like a big job for someone your age."

Hiccup looked thoughtful and nodded. "It's an important one, though. Someone's gotta do it," he answered. After a few seconds of silence, he spoke again. "Jack, can I see your staff? I'm wondering if it's some sort of magical object, especially since you don't seem to know exactly how you're doing what you're doing."

Jack looked at the staff he was holding. It was plain wood, curved into a hook at one end. Where he touched it, as well as some other spots along its surface, frost covered the wood. This being the source of his power would make sense, since he had used it to create the frost on the trees and pond. The thought disappointed him a little- he had thought maybe he had special ice powers, not that he just happened to have a staff that gave him powers. Either way, it felt like it belonged in his hands, like it was a part of him. He looked up at Hiccup, who had just a moment ago been standing there looking a great deal more intimidating than him, with a dragon and a sword he looked like he knew how to use.

Hiccup waited. If Jack actually gave him his staff, he would be 100% convinced that Jack didn't mean any harm, and that he was just a confused teenager who had happened to find a magical object. Being himself a confused teenager who had happened to find a magical creature, he could relate. The way Jack held the staff made it look like he'd had it for years, which clashed with the implication that he didn't really know how to use it. The entire situation was beyond strange, and Hiccup realized that he didn't really have any right to ask for the staff, but he wanted to figure out what was going on.

Jack realized, as Hiccup stared at him expectantly, that he didn't really want to give him the staff. It was his, and he felt like he should protect his right to have it. That being said, he was beginning to wonder if Hiccup was one of those people he needed to bring joy to. Hiccup had taken a huge responsibility upon himself, and he appeared to travel alone, with the exception of the dragon. If Jack was right about the sadness he sensed, Hiccup could do with some joy, and a friend. He seemed like a good guy who just needed to be a bit more trusting.

"All right," Jack said after some deliberation. "I trust you."

Jack held out the staff to Hiccup, expertly spinning it around so that the side without the hook was facing Hiccup. Hiccup took it, and he noticed immediately that the frost that had been covering the wood disappeared the moment Jack let go. As Jack watched, Hiccup closed his eyes for a moment and concentrated on activating the spell that allowed him to view magic. When he opened his eyes again, the staff looked just as it had earlier—a plain piece of wood. It wasn't magic, which actually interested Hiccup more that it would have it if had been magic. He moved to hold the staff back out for Jack to take, but when he looked up he was momentarily blinded by the blaze of light coming from Jack. Blinking a few times, he concentrated on identifying the type of magic radiating from the teenager who stood near. Eventually, Hiccup was able to tell two things for certain. Jack's magic was cold, and though it was also something else he couldn't quite identify, it was undeniably _good_.

"Well, your staff isn't magic, but you sure are," Hiccup said after he'd held the staff for about 30 seconds. "I can also tell that you're a good person, and I'm sorry for treating you like that earlier." Hiccup held the staff out, and Jack took it back gratefully. The moment Jack touched it again, Hiccup could see that the staff glowed with the same power infusing Jack. _Interesting—his staff is only magic for him_ , Hiccup thought.

"Thanks, Hiccup. Are we good now?" Jack asked.

"Yeah, we're good." Hiccup smiled, and Jack noticed that it lowered how intimidating he was by about ten notches.

"So… I don't know where you're going, but can I come with you?" Jack blurted suddenly. "Now that you're not worried I'm going to wreck the environment, you seem pretty cool. Plus I don't really have anywhere else to go."

Hiccup thought about this for a second, and added some more interesting things about Jack to his thoughts. He was barefoot, for one. He also didn't have a pack or any sort of personal items besides his staff, and he had white hair. He could control ice, and didn't seem bothered by the cold. He wasn't human, or not fully, he couldn't be. Maybe this was some new race from the Arctic climates no one knew about? He was teeming with magic, but didn't seem to understand how to control it fully. There was something going on here, and Hiccup was more than curious enough about it to let Jack tag along with him for a while. Besides, he was getting lonely with only Toothless around. And strangest of all, Jack seemed like he didn't know what else to do.

"Yeah, sure, you can tag along. It'll be nice to have the company." Hiccup responded.

"Great!" Jack said. "Lead the way."

Hiccup didn't argue and started off toward Burgess once again, with Jack and Toothless following along behind. He had a lot of questions he wanted to ask Jack, and eventually he couldn't hold out any longer. "Jack?" he asked, "Where is all your stuff? There's no way you should just be sleeping outside barefoot with nothing to eat, and if you have nowhere to go, how did you get here?"

Jack looked at Hiccup and shrugged. "This is all I have. And I honestly have no idea."

Hiccup figured Jack just didn't want to tell him about his past, and he understood that. He hadn't told anyone about his past. He was still curious, but he'd have to wait until Jack felt comfortable enough to tell him. If he stayed with him, that is. They continued on toward Burgess, stopping again only for Hiccup to tell Toothless to meet them at the far side of the large town and to stay out of sight. After Toothless left, Jack grinned and asked his big question.

"So what's with the dragon?"


	4. The Big Four Unite

**Author's Note: Hey again everyone! Thanks so much to everyone who reviewed, followed, and favorited! I know I say that a lot, but knowing that people are enjoying this story makes me really happy. I especially enjoy reading reviews, they make my day! Please feel free to comment, theorize, or just talk to me about the story!**

 **Review Replies:**

 **BrawlerGamer: I also really like the relationship between Hiccup and Jack, more is coming, I promise! Thanks for reviewing, I appreciate you always telling me your thoughts!**

 **mcarno: Thanks so much, I'm glad you enjoyed it!**

Rapunzel wandered around in the wilderness for what seemed like forever before she finally came upon a settlement. As luck would have it, the settlement was fairly large, and she was pretty sure she'd be able to find what she needed. However, there was still the issue of money. Growing up in the tower, she had never needed to use money, and so she wasn't sure what the average prices for things were. Rapunzel had taken what Gothel had on her before she'd left the tower, but she assumed Gothel kept most of her money elsewhere. With a grand total of 8 gold pieces, 12 silver pieces, and 2 copper pieces, Rapunzel hoped she would be able to afford what she needed.

The people in the town were friendly, and after asking someone Rapunzel learned that the town was called Burgess. Remembering first that she needed some new clothes, Rapunzel asked someone else where the best place to find clothes was. When she found the place the townsperson had recommended, she took some time to browse, eventually purchasing a simple outfit consisting of breeches, a shirt, boots, a belt, and a cloak. The shirt was a nice shade of lavender that matched the dress she was wearing, and the rest of the outfit was in varying shades of brown. It seemed study enough for adventuring, and though she knew many adventurers wore armor, she doubted she had enough money to buy any for herself. The first step, she figured, was getting an outfit that would be comfortable for traveling.

Those she talked to were friendly, but she could tell they were very curious about her hair. The more stares she attracted, the more uncomfortable Rapunzel felt. Try as she might to forget, she remembered Gothel telling her that those beyond the tower walls would try to use her hair's power for themselves. As she thought about it, Rapunzel realized how ironic it was that Gothel had told her of the selfishness of others while using her hair's power to stay young.

Gothel had told her that she was special—that being able to reverse aging as she could was very rare. Rapunzel didn't doubt that there were other people out there who wanted that power for themselves, but she also knew that there were kind, selfless people out there too. Eugene had proven that to her beyond a shadow of a doubt. Gothel was wrong about the world, and Rapunzel was sure that she'd find kind people to travel with if she just looked.

With that thought in mind, Rapunzel ignored the stares. Hair as long as hers was very unusual, and she knew that the townsfolk didn't mean to make her uncomfortable. Pascal kept making faces at the people who were staring, and she had to admit that if it hadn't been her they were staring at, it would've been really funny. She continued exploring the village in search of the rest of the things she needed, and eventually she found her way to the marketplace.

Although she knew she needed to hurry, Rapunzel couldn't help but marvel at the variety of items being sold at the marketplace. The first vendor she saw was selling weapons, and their wares ranged from simple swords to greataxes to crossbows. All of the weapons looked like they'd be very dangerous in the right hands.

"Do you need help finding anything?" The weapons vendor spoke up from behind a rack. Rapunzel could tell from his amused expression that he was asking more to be polite than because he actually thought she was going to buy something. He was an older man, and he paid no attention to Rapunzel's hair heaped in her arms, tangled around the outfit she'd bought. He looked like someone who had seen everything once or twice and was no longer surprised by anything life threw at him.

"No, thank you though," Rapunzel answered. "I'm a bit clumsy, and it probably wouldn't be the best plan for me to own something I could put my eye out with." She grimaced as she thought about how she'd clonked herself on the head with her pan when she'd first met Eugene.

The vendor smiled. "You never know. Maybe you just need some practice."

Rapunzel smiled brightly. "I sure hope so!" She continued on through the marketplace, spending most of the rest of her money on a sturdy leather backpack, a bedroll and blanket, a belt pouch, some food, and a waterskin, leaving her with 6 silver and 2 copper pieces. She also managed to find a map of the surrounding area, which she figured would come in handy. Satisfied, Rapunzel shouldered her new backpack, filled with the items she'd bought, and started looking for people who might be willing to travel with her and adventure.

That turned out to be easier said than done, because it was hard to tell whether someone was an adventurer, or if they just carried a weapon. Rapunzel decided against asking a passing elf because she was sure she was ignorant of some important custom that was necessary for talking to the other race. There weren't many dwarves around, though she didn't know why, and she kept accidentally mistaking gnomes and halflings for children. Rapunzel decided to stick with asking other humans, just to be safe.

Her hair was still earning her an uncomfortable amount of strange looks, and she was about to pull out her cloak to try and to stuff it in the hood when she saw exactly who she'd been looking for. Not only was the girl armed, she was also dressed in traveling clothes and leading a horse. And best of all, she too had unusual hair— her bright red mop of curls was getting her almost as many looks as Rapunzel's 70-foot-long golden hair was. Well, maybe not almost as many, but they both had unusual hair for the area, and Rapunzel was taking anything she could get right now. With Pascal urging her on, she walked up to the other girl.

"Um… excuse me?" Rapunzel tapped on the redhead's shoulder to get her attention. Being closer allowed Rapunzel to notice that not only did the other girl have a longbow, but she also had a sword sheathed at her side.

"Yes?" The girl turned around to face Rapunzel, tugging on her horse's reins as she did so to keep him from eating the weeds growing in between the cobblestones making up the pavement. When she saw Rapunzel, the redhead's eyes widened as they followed the long path the golden hair took from Rapunzel's head to the heap in her arms. "Wow lass, looks like your hair is even more of a hassle than mine," she said after a few moments.

"Yeah, maybe," Rapunzel replied sheepishly. "I'm sorry to bother you, and this is a weird question, but you seem like an outdoorsy person, and I'm looking for people to, um, adventure with me, in the literal sense of the word, and… I'm sorry, I'm mumbling. I am looking for people that might want to adventure with me and whoever else I find and you seemed like a good candidate." Rapunzel finished and looked at the redhead expectantly. "Oh, and I'm Rapunzel," she added quickly, sticking out her hand. "And this is Pascal, on my shoulder."

"I'm Merida, nice to meet you both," the other girl said, shaking Rapunzel's hand. "And this is a really weird coincidence, but I'm doing the exact same thing you are. I've been alone for a while and finding company has been my most recent goal. I'd be glad to go with you."

"Great!" Rapunzel exclaimed, grinning at Merida. "We've already got something in common," she lifted up a heap of her hair in one arm, "unmanageable hair." Merida laughed and blew aside a bang with mock anger.

"So what exactly do you do, if you don't mind me asking?" Merida asked Rapunzel. They'd found a bench that was unoccupied in a quieter part of the town and were getting to know each other better.

"I'm not totally sure, actually," Rapunzel admitted. "It's a long story, but I've always been able to heal people, and I just recently discovered that I can also do some other things. Someone called me a cleric, but I don't really know what that means."

"I don't know a whole lot about them, but I've heard that clerics are supposed to be people who channel the power of the gods here on Earth," Merida said. "They can heal people, so I guess it's possible that you could be a cleric. Maybe you should just wait and see what happens."

Rapunzel nodded. She liked Merida, she was funny and reminded her a bit of Eugene. She was also glad to have found another female first, as she'd only had major experience with one male.

"Is there a reason for the hair, or do you just like it being really long?" Merida continued. "It seems like it's probably more trouble than it's worth, if you ask me."

"Um…" Rapunzel hesitated. Her hair was what had gotten her locked up for her entire childhood, and it was why she was in this situation at all. That being said, if she was going to be fighting alongside Merida, she was going to find out sooner or later. Rapunzel had always been trusting, perhaps too much for her own good. Pascal shrugged, and so Rapunzel plowed on. "You know how I said I was a healer? Well, my hair has the ability to heal people, and… some other stuff. But if it gets cut, it turns brown and loses its power."

Merida was silent for a moment before she responded. "So you were kind of forced to grow it out, that's awful! I'm sure that knowing you can't—well I suppose you could but you wouldn't want to— makes you want to cut it even more."

Rapunzel was astounded. "You're not surprised? You don't think it's weird?"

"Oh, it's weird all right. But so is the world we live in. I mean, look at that guy over there with the pure white hair!" Merida pointed, and sure enough, there was a teenager with white hair by a shop in the marketplace. He was holding a staff and appeared to be barefoot.

"Huh," Rapunzel muttered, peeking down at her bare feet.

"Oh, crap!" Merida shrieked suddenly, jumping up and startling Angus. "I completely forgot to look for Hiccup!" She spared a second to soothe Angus and make sure he was still securely tied, and then she started walking quickly out toward the center of the town, where there were more people gathered around.

Rapunzel raised an eyebrow and got up to follow her, habitually gathering up her hair as she did so. "You mean, like the hiccups you get when you eat too fast?" she asked.

"No, there's a guy named Hiccup who's supposed to be around here, that's why I was here in the first place!" Merida explained hurriedly. "Help me look for a guy dressed kind of like me, in earth tones that looks like he lives in the woods."

"Um, okay," Rapunzel agreed. Looking back over towards where the white-haired boy was, she took a closer look at the guy that was with him. He had brown hair and was wearing a green shirt over brown pants. "How's that for earth tones?" she asked, pointing. "Look over at the guy that's with the white-haired guy from earlier."

"Come with me to ask him, even if it's not Hiccup maybe we can recruit him," Merida responded excitedly.

Rapunzel grinned. This was why she liked company— all these little things were so much fun. She missed Eugene, but she was on the right track to get him back, and he wouldn't be mad at her for having fun. She quickly followed Merida, weaving through the crowd to where the possible recruit was. As they walked up to where the two boys were standing, a snippet of their conversation could be heard.

"And I couldn't just let them kill him, you know? It wasn't fair," they heard the brunette say.

Curious, Merida motioned to Rapunzel and then whispered, "I know it's nosy but I want to hear what they're talking about. He said something about someone getting killed." Rapunzel nodded, and started to whistle in an attempt to appear casual while she and Merida pretended to be looking at fruit at a nearby stand.

"Yeah, that's a really bad situation. I think you did the right thing though. Maybe someday you can go back home, once it's been a few years, and talk to them about it. You know, leave Toothless an hour or two away where you know he'd be safe." The white haired teen finished talking and looked straight at Rapunzel. "You ladies need something?" he asked, leaning on his staff.

Merida and Rapunzel looked at each other and flushed a bright red. "Yes, sorry," Merida managed to get out. "I was wondering if your name happened to be Hiccup?" She looked at the brunette, expecting a confused no.

"Yeah, I'm Hiccup, how did you know?" the brunette answered.

"Oh, you are? What a lucky break! I'm Merida, and this is Rapunzel," Merida said, pointing to herself and the blond in turn. "I was just asking around about adventuring types and your name came up, so I figured I'd try and find you."

Hiccup and his companion exchanged a look. "I guess I could be considered an adventuring type," Hiccup said. "Why are you looking for adventurers?"

"Well, I've been by myself for a while, and it's been really lonely," Merida started. "My life lately has included a lot of fighting monsters, so I figured if I was going to find people to travel with they might as well be people who can fight monsters too."

Hiccup nodded. "That makes sense."

"Anyway," Merida continued, "Rapunzel and I have recently decided we want to try adventuring, and adventuring is safer and more fun in a group. So, I figured I'd ask you what you thought about the idea."

As Merida spoke, Rapunzel took a closer look at Hiccup's companion. He was unusually pale, and he had bright blue eyes. She glanced at his staff and couldn't help but notice what she thought was frost on it, but she quickly looked away.

"Well, some company does sound nice," Hiccup said. "I've been by myself for a while too, I just met Jack this morning. This is Jack, by the way." He motioned to the white-haired teenager he had been talking to earlier.

Jack waved at the two girls. "Hi, it's nice to meet you."

"It's nice to meet you too, Jack!" Rapunzel responded enthusiastically. "You can join us too, if you want!"

Jack grinned and turned to Hiccup. "What's the verdict, boss?" he asked. "Hanging out with these lovely ladies sounds like a pretty good idea to me."

Hiccup laughed. "You don't need to convince me! Three new friends in one day, I'm not going to know what to do with myself."

Jack stepped closer to the girls, putting a hand next to his mouth and leaning in dramatically. "Be careful though, if you're not nice to the trees Hiccup might have to destroy you," he whispered loudly.

Hiccup groaned. "You're never going to let that go, are you?"

Merida leaned toward Rapunzel and muttered "I'd like to see him try and destroy me." Rapunzel giggled.

Hiccup directed his attention back to the girls. "It'd be our pleasure to join your company."

"Yay!" Rapunzel squealed. Merida looked at her and laughed, then headed back to the bench where she had tied Angus and quickly tugged the end of the rope, undoing the knot. She then led her horse back to where the others were.

"Where are we going?" Rapunzel asked as the four moved out of the crowded marketplace. She was glad that someone else was leading the way, since she wasn't really sure where to go next. That being said, she was hoping to start getting a feel for the geography around where they were planning to travel. She was also glad that they were moving on quickly, since she wanted to put as much distance between her and Gothel as possible.

"Well, I've got to go and meet back up with someone in the forest before we can go anywhere else," Hiccup said. "From there I don't really have any big travel plans."

"Wait, I thought you said you'd been by yourself for a while," Merida said, confused.

Hiccup froze. "I guess you're right, I wasn't completely alone," he admitted. "It's just that I don't consider him to be the same sort of company as you guys. You'll… you'll understand when you meet him."

Jack snorted. "That's a bit of an understatement."


End file.
